A Critical (But Highly Sympathetic) Reading of New Yorkers’ Sexual Habits and Anxieties

From left: The Car Salesman in a Relationship With an Older Woman, 32, Brooklyn Heights; The Temporarily Celibate Actress, 23, Astoria; The Single Brooklyn Bartender, 23, Williamsburg; The Mailroom Worker in an On-Again-Off-Again Relationship, 35, Upper West Side.

(Photo: Joshua Allen; Grooming by Bryan Lynde)

So there’s this iPhone app called Grindr. It’s a GPS-enabled social-networking service for gay men. It tells you how many feet away a possible hookup is standing. Each profile comes with a picture, a tagline, the relevant stats, and a declaration of interest. You scroll through a column of heads and torsos arranged in descending order of proximity, tapping on the ones that seem promising and chatting with the ones who want the same things you do. As you make your way through the city, the menu of men reshuffles, and the erotic terrain updates in real time.

Has the search for erotic gratification ever been so efficient? Until recently, being a cad or coquette took a lot of work: You needed to buy a little black book, and you had to go around filling it, and then you had to schedule your calls for a time when the target of your seduction was likely to be at home. The less-self-assured daters in New York faced the sickening anxiety of the first phone call, or the cold approach in the bar. There were palliatives designed to help people cope—the newspaper personal ads, the paid dating services, the dirty videos and magazines—but they were generally understood to be the province of weirdos and losers.

No more. The social technologies that assist in dating and mating today are more than palliatives—they’ve changed the nature of the game. If the cold approach is more than you can deal with, put up a Craigslist ad, or join OkCupid, Manhunt, or Nerve. If the phone call makes you nervous, send a text message. And while you’re at it, send a text message to a half-dozen other people with everyone’s favorite late-night endearment: “where u at?” If nothing works out and you find yourself alone at home again, simply fire up XTube or YouPorn and choose from an endless variety of positions to help you reach a late-night climax.

Virtually everyone under the age of 30 has grown up with their sexuality digitally enhanced, and the rest of us are rapidly forgetting the world before we all were hooked into the same erotically charged network of instantaneously transmitted messages and images. This must be true across the country, but it seems particularly suited for a city as dense, morally libertine, and sexually spirited as New York. Part of the promise of this city has always been that there’s another prospective partner a subway stop away, but not until recently could that partner interrupt your daily business with a cell-phone snapshot of their parted thighs. And of course, the same technology that makes it easier to score also makes the sexual boast or confession easily transmissible to millions of other people.

Every Monday since April 2007, this magazine has posted on its Daily Intel blog a seven-day diary of an anonymous New Yorker’s sex life. It began as an experiment intended to entertain the bored at work, but the candor of the Diarists soon attracted an outsize and devout following. Since October 2007, they have been joined by a rambunctious cacophony of commenters as obsessive on the subject of sex as the Diarists themselves. They criticize, malign, offer support and tips, and digress into arguments about everyone else’s sex lives, as well as their own. The Diaries are often flooded with over 100 comments within 24 hours. Two months ago, the comments on one diary were closed down at 895.

Over the course of the Sex Diaries’ 132-week run, we have seen the city through the eyes of cuckolds and cheaters, sluts and prudes, victimizers and victims, starry-eyed lovers and detached pleasure seekers. We have followed aging women on dismal Craigslist dates, lonely gay men in pursuit of ostensibly curious straight guys, happily polyamorous couples, and co-dependent serial monogamists. We’ve watched some Diarists terrified of succumbing to their feelings and others unable to feel much of anything at all. We’ve watched a black man fly to meet a white couple at a T.G.I. Friday’s in the Midwest and have sex with the wife as the husband watched.

The Diaries can be arousing, a little. But in aggregate, they wound up doing something more interesting: They cracked open a window into the changing structure, rhythm, and rhetoric of sex in New York. The Diarists are a self-selecting group, of course: bizarrely oversharing New Yorkers motivated by the impulse to brag or, as often, the urge to fling their terrible abjection in the face of the world. But as we watched them struggle with the peculiar hazards of mating in New York today (failing spectacularly, or succeeding all too well), we saw that their hassles were everyone’s writ large, and their stories posed a question: Are the digital tools that make it easier to find sex compounding the confusion that accompanies it?